CN111018768A - Recovery method of N-methyl pyrrolidone - Google Patents
Recovery method of N-methyl pyrrolidone Download PDFInfo
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- CN111018768A CN111018768A CN201910258112.XA CN201910258112A CN111018768A CN 111018768 A CN111018768 A CN 111018768A CN 201910258112 A CN201910258112 A CN 201910258112A CN 111018768 A CN111018768 A CN 111018768A
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- methyl pyrrolidone
- filtrate
- reaction kettle
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- waste materials
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Abstract
The invention discloses a method for recovering N-methyl pyrrolidone, which comprises the following steps: 1) taking waste materials of lithium battery electrode materials, adding deionized water into the waste materials, stirring uniformly and soaking; crushing the waste materials, and performing ultrasonic dispersion during the crushing process to obtain a waste mixed solution; 2) adding a flocculating agent into the waste mixed liquid obtained in the step 1), stirring, standing and filtering to obtain solid floccules and a filtrate; 3) feeding the filtrate obtained in the step 2) into a reaction kettle, heating the filtrate in the reaction kettle, and fractionating the filtrate; 4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, heating the filtrate in the reaction kettle, and rectifying the N-methyl pyrrolidone crude liquid. The invention is beneficial to improving the quality of the subsequent fractionation of the N-methyl pyrrolidone; improves the recovery quality of the N-methyl pyrrolidone and is beneficial to saving energy.
Description
Technical Field
The invention relates to the technical field of recovery of N-methyl pyrrolidone, in particular to a recovery method of N-methyl pyrrolidone.
Background
N-methyl pyrrolidone is an important chemical raw material, belongs to a polar aprotic solvent, can be mixed and dissolved with water in any proportion, is almost completely mixed with all organic solvents (ethanol, acetaldehyde, ketone, aromatic hydrocarbon and the like), has strong polarity, low viscosity, strong dissolving capacity, small toxicity, strong biodegradability, excellent chemical stability and thermal stability, and is mainly applied to various industries such as petrochemical industry, plastic industry, medicines, pesticides, dyes, lithium ion battery manufacturing industry and the like.
In the production of the lithium battery industry, a large amount of N-methyl pyrrolidone is required to be used, the lithium battery needs to be scrapped after the service life is reached, and the N-methyl pyrrolidone in the lithium battery is recycled, so that certain economic benefit can be generated, and the ecological concept of environmental protection and green is met.
The existing N-methyl pyrrolidone method generally has the problems of high energy consumption, low recovery rate and the like in the recovery process, and usually higher energy is consumed to separate the N-methyl pyrrolidone from other waste liquid, so that not only is energy wasted, but also the separation is not clean enough, and the recovery quality of the N-methyl pyrrolidone is influenced.
Disclosure of Invention
The present invention is directed to a method for recovering N-methylpyrrolidone, which solves the above-mentioned problems of the prior art.
In order to achieve the purpose, the invention provides the following technical scheme:
a method for recovering N-methyl pyrrolidone comprises the following steps:
1) taking waste materials of lithium battery electrode materials, adding deionized water into the waste materials, uniformly stirring the waste materials, and soaking the waste materials for 1 to 2 hours; crushing the waste materials, and performing ultrasonic dispersion during the crushing process to obtain a waste mixed solution;
2) adding a flocculating agent into the waste mixed liquid obtained in the step 1), stirring, standing for 10-20min, and filtering to obtain solid floccule and filtrate;
3) feeding the filtrate obtained in the step 2) into a reaction kettle, heating the filtrate in the reaction kettle, keeping constant temperature when the temperature is raised to 120-;
4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, heating the filtrate in the reaction kettle, keeping constant temperature when the temperature is raised to 100-120 ℃, rectifying the N-methyl pyrrolidone crude liquid, and obtaining N-methyl pyrrolidone and a mixed liquid II after rectification.
As a further scheme of the invention: the addition amount of the deionized water in the step 1) is 1-2 times of the weight of the waste material.
As a still further scheme of the invention: the addition amount of the flocculating agent in the step 2) is 0.1-0.2 times of the total weight of the waste mixed liquor.
As a still further scheme of the invention: the flocculating agent in the step 2) is one or more of polyaluminium chloride, polyaluminium sulfate, polyferric chloride and polyferric sulfate.
As a still further scheme of the invention: the ultrasonic frequency in the step 1) is 40-60 KHz.
As a still further scheme of the invention: and 2) vacuumizing the reaction kettle before heating the reaction kettle to reduce the pressure in the reaction kettle to 10-20 KPa.
As a still further scheme of the invention: and 3) vacuumizing the reaction kettle before heating the reaction kettle to reduce the pressure in the reaction kettle to 5-10 KPa.
Compared with the prior art, the invention has the beneficial effects that:
according to the invention, the waste material is pretreated, the N-methyl pyrrolidone is dissolved in water by adopting ultrasonic dispersion, and impurities in the N-methyl pyrrolidone aqueous solution are primarily removed by adopting a flocculant adding mode, so that the quality of subsequent N-methyl pyrrolidone fractionation is improved;
the whole boiling point of the aqueous solution is improved by adopting a pressure reduction mode, so that the heat energy consumed in the fractionation process of the solution is greatly reduced, and the energy is saved;
the rectification treatment ensures that the purity of the N-methyl pyrrolidone is higher, reduces impurities in the N-methyl pyrrolidone, and further improves the recovery quality of the N-methyl pyrrolidone.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A method for recovering N-methyl pyrrolidone comprises the following steps:
1) taking waste materials of lithium battery electrode materials, adding deionized water which is 1 time of the weight of the waste materials, uniformly stirring, and soaking for 1 hour; crushing the waste materials, and dispersing the crushed waste materials by using ultrasonic waves with the frequency of 40KHz to obtain waste material mixed liquor;
2) adding polyaluminium chloride which is 0.1 time of the total weight of the waste mixed liquor into the waste mixed liquor obtained in the step 1); stirring, standing for 10min, and filtering to obtain solid floccule and filtrate;
3) sending the filtrate obtained in the step 2) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 10KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is increased to 120 ℃, fractionating the filtrate, and obtaining N-methylpyrrolidone crude liquid and mixed liquid I after fractionation;
4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 5KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is increased to 100 ℃, rectifying the N-methyl pyrrolidone crude liquid, and obtaining N-methyl pyrrolidone and a mixed liquid II after rectification.
Example 2
A method for recovering N-methyl pyrrolidone comprises the following steps:
1) taking waste materials of lithium battery electrode materials, adding deionized water which is 2 times of the weight of the waste materials, uniformly stirring, and soaking for 2 hours; crushing the waste materials, and dispersing the crushed waste materials by ultrasonic waves with the frequency of 60KHz to obtain waste material mixed liquor;
2) adding polymeric ferric sulfate which is 0.2 time of the total weight of the waste mixed liquor into the waste mixed liquor obtained in the step 1); stirring, standing for 20min, and filtering to obtain solid floccule and filtrate;
3) sending the filtrate obtained in the step 2) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 20KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is raised to 140 ℃, fractionating the filtrate, and obtaining N-methylpyrrolidone crude liquid and mixed liquid I after fractionation;
4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 10KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is increased to 120 ℃, rectifying the N-methyl pyrrolidone crude liquid, and obtaining N-methyl pyrrolidone and a mixed liquid II after rectification.
Example 3
1) Taking waste materials of lithium battery electrode materials, adding deionized water which is 1.5 times of the weight of the waste materials, uniformly stirring, and soaking for 1.5 h; crushing the waste materials, and dispersing the crushed waste materials by ultrasonic waves with the frequency of 50KHz to obtain waste material mixed liquor;
2) adding a flocculating agent which is 0.15 time of the total weight of the waste mixed liquor into the waste mixed liquor obtained in the step 1), wherein the flocculating agent is formed by mixing polyaluminium sulfate and polyferric chloride according to the weight ratio of 1: 3; stirring, standing for 15min, and filtering to obtain solid floccule and filtrate;
3) sending the filtrate obtained in the step 2) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 15KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is raised to 130 ℃, fractionating the filtrate, and obtaining crude N-methylpyrrolidone liquid and mixed liquid I after fractionation;
4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 7KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is raised to 110 ℃, rectifying the N-methyl pyrrolidone crude liquid, and obtaining N-methyl pyrrolidone and a mixed liquid II after rectification.
Example 4
A method for recovering N-methyl pyrrolidone comprises the following steps:
1) taking waste materials of lithium battery electrode materials, adding deionized water which is 1.5 times of the weight of the waste materials, uniformly stirring, and soaking for 1.5 h; crushing the waste to obtain waste mixed liquor;
2) adding a flocculating agent which is 0.15 time of the total weight of the waste mixed liquor into the waste mixed liquor obtained in the step 1), wherein the flocculating agent is formed by mixing polyaluminium sulfate and polyferric chloride according to the weight ratio of 1: 3; stirring, standing for 15min, and filtering to obtain solid floccule and filtrate;
3) sending the filtrate obtained in the step 2) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 15KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is raised to 130 ℃, fractionating the filtrate, and obtaining crude N-methylpyrrolidone liquid and mixed liquid I after fractionation;
4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, vacuumizing to reduce the pressure in the reaction kettle to 7KPa, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is raised to 110 ℃, rectifying the N-methyl pyrrolidone crude liquid, and obtaining N-methyl pyrrolidone and a mixed liquid II after rectification.
Example 5
A method for recovering N-methyl pyrrolidone comprises the following steps:
1) taking waste materials of lithium battery electrode materials, adding deionized water which is 1.5 times of the weight of the waste materials, uniformly stirring, and soaking for 1.5 h; crushing the waste materials, and dispersing the crushed waste materials by ultrasonic waves with the frequency of 50KHz to obtain waste material mixed liquor;
2) adding a flocculating agent which is 0.15 time of the total weight of the waste mixed liquor into the waste mixed liquor obtained in the step 1), wherein the flocculating agent is formed by mixing polyaluminium sulfate and polyferric chloride according to the weight ratio of 1: 3; stirring, standing for 15min, and filtering to obtain solid floccule and filtrate;
3) feeding the filtrate obtained in the step 2) into a reaction kettle, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is raised to 130 ℃, fractionating the filtrate, and obtaining crude N-methylpyrrolidone liquid and mixed liquid I after fractionation;
4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, heating the filtrate in the reaction kettle, keeping the temperature constant when the temperature is raised to 110 ℃, rectifying the N-methyl pyrrolidone crude liquid, and obtaining N-methyl pyrrolidone and a mixed liquid II after rectification.
According to the invention, the waste material is pretreated, the N-methyl pyrrolidone is dissolved in water by adopting ultrasonic dispersion, and impurities in the N-methyl pyrrolidone aqueous solution are primarily removed by adopting a flocculant adding mode, so that the quality of subsequent N-methyl pyrrolidone fractionation is improved; the whole boiling point of the aqueous solution is improved by adopting a pressure reduction mode, so that the heat energy consumed in the fractionation process of the solution is greatly reduced, and the energy is saved; the rectification treatment ensures that the purity of the N-methyl pyrrolidone is higher, reduces impurities in the N-methyl pyrrolidone, and further improves the recovery quality of the N-methyl pyrrolidone.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (7)
1. A method for recovering N-methylpyrrolidone is characterized by comprising the following steps:
1) taking waste materials of lithium battery electrode materials, adding deionized water into the waste materials, uniformly stirring the waste materials, and soaking the waste materials for 1 to 2 hours; crushing the waste materials, and performing ultrasonic dispersion during the crushing process to obtain a waste mixed solution;
2) adding a flocculating agent into the waste mixed liquid obtained in the step 1), stirring, standing for 10-20min, and filtering to obtain solid floccule and filtrate;
3) feeding the filtrate obtained in the step 2) into a reaction kettle, heating the filtrate in the reaction kettle, keeping constant temperature when the temperature is raised to 120-;
4) feeding the N-methyl pyrrolidone crude liquid obtained in the step 3) into a reaction kettle, heating the filtrate in the reaction kettle, keeping constant temperature when the temperature is raised to 100-120 ℃, rectifying the N-methyl pyrrolidone crude liquid, and obtaining N-methyl pyrrolidone and a mixed liquid II after rectification.
2. The method for recovering N-methylpyrrolidone according to claim 1, wherein the deionized water added in step 1) is 1-2 times of the weight of the waste material.
3. The method for recovering N-methylpyrrolidone according to claim 2, wherein the amount of the flocculant added in step 2) is 0.1-0.2 times of the total weight of the mixed liquid of the wastes.
4. The method for recovering N-methylpyrrolidone according to claim 3, wherein the flocculant in step 2) is one or more of polyaluminium chloride, polyaluminium sulfate, polyferric chloride and polyferric sulfate.
5. A process according to any one of claims 1 to 4, wherein the ultrasonic frequency in step 1) is 40 to 60 KHz.
6. A method as claimed in any one of claims 1 to 4, wherein step 2) is carried out by evacuating the reaction vessel before heating the vessel to reduce the pressure in the vessel to 10 to 20 KPa.
7. A process according to claim 6, wherein in step 3) the pressure in the reaction vessel is reduced to 5 to 10KPa by applying a vacuum before heating the reaction vessel.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910258112.XA CN111018768A (en) | 2019-04-01 | 2019-04-01 | Recovery method of N-methyl pyrrolidone |
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| CN201910258112.XA CN111018768A (en) | 2019-04-01 | 2019-04-01 | Recovery method of N-methyl pyrrolidone |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112279797A (en) * | 2020-10-28 | 2021-01-29 | 重庆工商大学 | Method for recovering N-methyl pyrrolidone from polyurethane adhesive cleaning waste liquid |
| CN113173875A (en) * | 2021-05-12 | 2021-07-27 | 南京长江江宇环保科技有限公司 | Method for recycling N-methyl pyrrolidone from waste anode electrode slurry in lithium battery production |
| CN115367906A (en) * | 2022-07-04 | 2022-11-22 | 浙江南都电源动力股份有限公司 | Method for recovering NMP cleaning waste liquid of lithium battery |
| WO2023000844A1 (en) * | 2021-07-23 | 2023-01-26 | 广东邦普循环科技有限公司 | Method for recycling waste battery slurry |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102544627A (en) * | 2010-12-29 | 2012-07-04 | 比亚迪股份有限公司 | Method for recycling N-methyl-2-pyrrolidone from lithium battery electrode material |
-
2019
- 2019-04-01 CN CN201910258112.XA patent/CN111018768A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102544627A (en) * | 2010-12-29 | 2012-07-04 | 比亚迪股份有限公司 | Method for recycling N-methyl-2-pyrrolidone from lithium battery electrode material |
Non-Patent Citations (2)
| Title |
|---|
| 张晋霞等: "《含锌冶金尘泥分选理论及应用》", 31 December 2017 * |
| 沈众等: "锂电池回收液NMP精馏小试研究", 《环境科技》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112279797A (en) * | 2020-10-28 | 2021-01-29 | 重庆工商大学 | Method for recovering N-methyl pyrrolidone from polyurethane adhesive cleaning waste liquid |
| CN112279797B (en) * | 2020-10-28 | 2022-07-22 | 重庆工商大学 | Method for recovering N-methyl pyrrolidone from polyurethane adhesive cleaning waste liquid |
| CN113173875A (en) * | 2021-05-12 | 2021-07-27 | 南京长江江宇环保科技有限公司 | Method for recycling N-methyl pyrrolidone from waste anode electrode slurry in lithium battery production |
| WO2023000844A1 (en) * | 2021-07-23 | 2023-01-26 | 广东邦普循环科技有限公司 | Method for recycling waste battery slurry |
| CN115367906A (en) * | 2022-07-04 | 2022-11-22 | 浙江南都电源动力股份有限公司 | Method for recovering NMP cleaning waste liquid of lithium battery |
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Application publication date: 20200417 |